Tributyltin Chloride → 1-methyl-3-tributylstannanyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

3-Iodo-1-methyl-1H-indazole (0.15 g, 0.58 mmol) was dissolved in THF (3 ml) and the solution was cooled to −16° C. using a NaCl/ice bath. Isopropylmagnesium chloride (2.0M in THF, 0.32 ml, 0.64 mmol) was added dropwise and the reaction mixture was stirred at −16° C. for 15 min. Tributylchlorostannane (0.18 ml, 0.66 mmol) was slowly added and the reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography over silica gel with EtOAc/Hexanes (0.5% triethylamine, gradient 0-5% EtOAc) to give 224 mg (92%) of 1-methyl-3-tributylstannanyl-1H-indazole as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.70 (d, J=8.3 Hz, 1H), 7.32-7.45 (m, 2H), 7.11 (ddd, J=8.0, 6.3, 1.5 Hz, 1H), 1.52-1.69 (m, 6H), 1.19-1.44 (m, 12H), 0.83-0.95 (m, 9H).

Provenance & Evidence